Dan Humphrey
Daniel Randolph "Dan" Humphrey is the main character in ''Gossip Girl'' and the TV Series of the same name. The character is portrayed by actor Penn Badgely in the television series Gossip Girl. Novel Series Dan Humphrey is the son of Rufus Humphrey and has a younger sister, Jenny Humphrey. His absent mother, who ran off with a European aristocrat, returns to support Dan when she hears of his sexual confusion. Dan and his family live on the liberal-cultured and artistic Upper West Side, the alternative of the old moneyed and conservative Upper East Side. He attends the Riverside Preparatory School for Boys, where wealthy playboy Chuck Bass attends, as a scholarship student. At the end of the series, he matriculates to Evergreen State College in Washington. He is described as being attractive and sensitive, loves to write poetry, and one of his poems, Sluts, was featured in The New Yorker. He revealed his favorite word is “'death'” and drinks copious amounts of dark coffee and chain smokes cigarettes. He over analyzes and is easily frustrated. Dan is very close and protective of little sister Jenny who attends an exclusive private school, called the Constance Billard School for Girls, a small, elite, all-girls school located at 93rd and Madison Avenue. Television Series Son of rocker Rufus and artist Alison, Dan is the oldest of their two children. He had a crush on Serena van der Woodsen from the age of fifteen and was one of the kindest to her when she returned from boarding school. He is attractive but he often felt beneath his rich classmates. In Season 1 especially he was extremely protective of his younger sister Jenny, he was especially concerned when she decided to become a part of Serena's ex-best friend Blair's group which involved her spending a lot of her time pleasing the Queen Bee. His most noted relationship is often seen as his Season 1 & 2 on-again, off-again relationship with Serena. He remains close to his now step-sister and is always at her side when she needs help, he said he will always be there for Serena. He is best friends with Nate Archibald the rich son of Howard and Ann Archibald. He is also now best friends with Blair Waldorf and has fallen in love with her. He has also got closer to Chuck and become his friend. Background Dan "Lonely Boy" Humphrey is the son of rocker Rufus Humphrey and artist Alison Humphrey, and is the older sibling of Jenny Humphrey. Dan is a poet and used to attend the St. Jude’s School for Boys with enemy Chuck Bass and previous rival for his love interest and now best friend Nate Archibald. Although accepted to Yale, he now attends NYU. He used to long for Serena van der Woodsen since a party when they were in ninth grade, and she was the only person who talked to him. He used to despise Serena’s best friend, Blair Waldorf; but became best friends with her, and is now in love with her. Dan and his family reside in Williamsburg, Brooklyn, and he wishes to attend Dartmouth College, a fact that is changed in later episodes when he shows interest in Yale. He was best friends with Vanessa Abrams whom he also dated before she left New York. Dan is clever, witty and patient; he works hard for what he wants and normally achieves his goals. He secretly has a desire to be on the "inside" of social cliques but does not reveal that to anyone in fear of becoming an even greater outcast. Although unexperienced with plotting and manipulation, he demonstrates promise when scheming with Blair. Season 1 Dan is introduced as a resident of Brooklyn, a poet who aspires to attend Dartmouth College. He attends St. Jude's School for Boys, but as he is financially lower-class in comparison to his rich Manhattan classmates, he is something of an outsider and tends to be ignored by everyone. He lives with his younger sister Jenny and father Rufus, who is separated from his mother. He has had a crush on the Upper East Side's former It Girl Serena van der Woodsen for several years, and is one of the first people to personally see her back in New York. He walked into her at a bar, causing her to drop her purse and spill things. In her haste to leave after being assaulted by Chuck Bass, Serena leaves her cellphone behind. The following morning, Dan goes to the hotel where Serena is living to return her cellphone. To get out of the Kiss on the Lips 'party being held by Blair Waldorf, Serena goes out on a date with Dan. They first went to Rufus's concert, but the date was interrupted when Jenny sent multiple text messages to Dan asking for help. When Dan and Serena went to investigate, they found a protesting Jenny being attacked by Chuck. Consequently, Dan punches Chuck, who shortly afterwords tells Serena that her life is over. After an awkward end to the date, Serena and Dan go out again, but have a fight when he finds out about Serena's one night stand with Nate Archibald, Blair's boyfriend. This was the reason she left boarding school, and Dan and Serena make up. Vanessa Abrams, Dan's best friend, suddenly returns. Jealous of Serena and still in love with Dan, Vanessa tries to show him that she is a better choice than Serena and her glitzy lifestyle. Dan is oblivious, but Serena notices and is made uncomfortable. She also becomes worried when she finds out about Dan's mother's return from Vanessa instead of Dan himself. Dan's choice is made clear when he and Serena sleep together for the first time at Christmas. A few weeks later, Dan goes to see what Jenny is doing. She has her laptop open to the Gossip Girl site, and hastily closes it before Dan can see. Rufus also walks over, suspicious of Jenny's odd behavior, and she is forced to show them what she was looking at: pictures of Serena buying a pregnancy test. Rufus is extremely upset over the possibility of Dan being a teenage father. Realizing the child could be his, Dan confronts confronts Serena. She lets him know that she was actually buying the test for Blair, who turns out not to be pregnant. Dan calms down but feels awkward, as he blurted out that he loved Serena and she only responds with 'okay'. It's not the response he was looking for and causes him to have some doubts. Later, Serena asks why he loves her, and after telling her, she says she loves him too. Georgina Sparks returns to the Upper East Side after rehab in Switzerland. She used to be a close friend of Serena, and the two of them got into a lot of trouble together - partying, drinking and doing drugs. Georgina is confused and annoyed to see Serena has changed her ways and doesn't want anything to do with her, but spikes her drink when the two of them go out to talk. This leads to Serena partying all night, then waking up remembering nothing, and missing her SATs which she later retook. All of this she hid from Dan, as Georgina was blackmailing her with a dark secret that she and Serena shared. Georgina later decides to get revenge by getting close to Dan, pretending to be 'Sarah', a new girl in town who doesn't know her way around. Clueless, Vanessa and Dan become best friends with 'Sarah'. Serena goes into a downward spiral, and lies to Dan, telling him that she slept with someone else. He breaks up with her and leaves, saying "I'm done." Serena absolves the guilt over her secret - a year ago, she suggested she and a drug addict called Pete do some coke. This was to put off sleeping with him. However, when Pete followed Serena's instructions and did a line, he overdosed and died. Even though Serena called 911, she has held herself responsible ever since. When Pete's parents told her they didn't blame her for what happened, Serena goes to a concert featuring Rufus's band with the intention of telling Dan everything and mending their relationship. She just misses seeing him, and when Georgina (still pretending to be Sarah) finds out that her intentions of blackmail are now invalid, she pulls Dan into the street and they kiss, with Dan completely unaware that Serena is at the concert. The next day, it is revealed that although Georgina spent the night with him, they didn't sleep together, but they may have well as. He is recruited by Blair Waldorf to help bring down Georgina, which he does by bringing Georgina to a park where Blair takes her down. He attends Lily and Bart's wedding as Serena's date where he breaks up with Serena for not being honest with him. The end of season shows Dan and Vanessa (who also just broke up with Nate) talking about what happened, possibly alluding to a Dan/Vanessa relationship. Season 2 According to Gossip Girl, over the summer Dan went from "'Lonely Boy to Playboy". Dan occupied himself by having continuous dates throughout the summer, with Serena still on his mind. Due to Dan's emotional complications, he is unable to complete an essay he was to submit. This ultimately results in his being fired due to his lack of commitment. Upon being fired from his summer job, he heads to the Hamptons upon realizing that he has been missing Serena. He hopes that by seeing Serena he will realize that they made the right decision, and he can move on. He arrives in the Hamptons, at the annual White Party, to find Serena and Nate in a passionate kiss. This reveals his true feelings for Serena as he shows obvious anger towards Serena's "cheating". Serena tries to convince him that she kissed Nate so as to make Nate's girlfriend (an older, married woman who was also paying him for being with her) jealous. Dan goes to leave, when he is confronted by a pair of girls he had dated throughout the summer. The girls, having found out about one another's relationships with Dan, pour their drinks on Dan and leave. Having been caught out by Serena for his hypocrisy, Dan and Serena retreat into the house to talk. They decide to meet up later at the beach, where they spend the night together. The following morning, Serena and Dan decide to halt any discussions on their relationships until they are back in the city. After some confusion between who was to take the train and who was to take the bus, they both ended traveling back to the city on the bus. This creates tension between the two, and as Serena gets up to use the bus bathroom, she trips and falls on Dan. She pulls up Dan and the two go into the bathroom to "fool around". The two decide to keep their rekindled relationship a secret until they were sure of themselves. Back in the city at Blair's "Welcome Back" party, Nate discovers the two in an embrace, revealing publicly that their relationship is "back on". In "The Dark Night" during the city-wide blackout, Dan and Serena talk about their problems while they were both trapped in an elevator. After a long talk (and a bit arguing), they realized they keep having the same fight, and break up. During their return to school, Serena and Dan are now friends until he meets a transfer student named Amanda Lasher. They share the same interests and have perfect chemistry. Blair attempts to keep them separate by making her one of her entourage so that Serena wouldn't have to suffer seeing them together and so she also wouldn't have to lose the competition of rebounding. Serena meets Amanda and nearly makes a fool out of herself. Blair forces Amanda to join them for lunch. Dan, thinking that Serena is trying to keep him away from Amanda gets Serena, who was reasoning with Dan why it happened, irritated when he kept implying that she was the one who forced her to lunch. Dan and Amanda's relationship goes public much to Serena's irritation. Serena then invites Dan and Amanda to go out later that night which turns into as disaster as Dan and Amanda continue to make her feel out of place. Isabel and Penelope, after witnessing Dan go out with Amanda that led to the relationship getting public, offers Serena several suitors, one in particular is a Dalton lacrosse team captain. Serena's new suitor fails to impress Dan. Dan thinks that Serena used the lacrosse team to rub it in his face. Later on, Penelope ruins Amanda's hair with a little help from Chuck. Dan runs to Amanda's aid who brushes him off saying that she no longer wants to see him. Dan gets into an argument with Serena and leaves. The next day, he is shunned because of Serena's rise to Queen Bee status. Dan's recommendation from Noah Shapiro, a writer, leads him to find new inspiration in the form of Chuck Bass. Noah suggests he use Chuck to fuel a new story. Dan does so and loses his shoes in the process. He ends up creating the character of 'Charlie Trout', a character that impresses Noah and asks him to find out what makes him tick. That night, Chuck mistakes a woman of being a prostitute and nearly gets punched until Dan defends him. The two end up in jail and Chuck confesses that he thinks his father hates him because he thinks he killed his mother at Chuck's birth. Chuck gets out of jail with some help from his lawyers and discovers Dan's reason as to why he was hanging out with him. Chuck gets angry at Dan and leaves him, saying that he lied about his mother's death and that she died in the Andes in a plane accident. Dan calls Noah Shapiro who bails him out. Dan confesses that he thinks it's wrong to exploit people for art and that he'd rather be safe. The two part ways and on bad terms. During a visit to Yale, Dan's recommendation for Yale admission goes awry as his only recommendation came from J.L. Hall. Jeremiah Harris and Noah Shapiro likely declined to write for Dan's recommendation. The Dean of Admissions suggests that he find someone to read his work. Dan then finds out Nate used his name to get into a fling with Jordan, a co-ed girl who eventually helps Dan get his work to other literature professors. Dan is stripped of his clothes and tied to a statue by members of the Skull & Bones after Chuck fools them into thinking he is Nate. Chuck's revenge on Dan then backfires on Chuck who loses Nate as a friend after Nate finds out about what he did to Dan. Dan and Nate begin a friendship much to Chuck's chagrin. During an invite to play soccer, Dan tries to visit Nate at his house and finds out about Nate's financial situation. Nate has been squatting in his own house that got seized amongst other property of the Archibalds. Dan invites Nate to a family dinner and tells Nate that he knows about Nate squatting in his own house. Nate leaves angry. Rufus talks to Dan and tells him that Nate needs help even if he doesn't want it, seeing as Nate has no one to turn to for help. Dan finds Serena outside Nate's house and repairs their relationship. The two become friends. Dan convinces Nate, who moves in after his house got seized. With Blair's situation with Chuck now out of hand, Serena gets Dan to help Blair and tells her that wearing him down would help her situation. Later on, he continues to help Blair by telling her that she should intercept him at home. With Blair desperate, he tells Blair that she should take a risk and say those '3 words, 8 letters' anyway. During Aaron's opening at Rufus' gallery, Vanessa confesses that Blair and Chuck used her in one of their sick games. Dan ruins Blair's opportunity to tell Chuck that she loves him and tells Serena what happened. He said that the two were bound to break up eventually and that what they did to Vanessa was sick. Serena says that Vanessa's matter is different and that Chuck and Blair do love each other. He later apologizes to Serena and get into an honest conversation. Serena confesses her feelings for Aaron and Dan gives her his blessing to date other people. Aaron and Serena start to date each other while Dan realizes that he still has feelings for Serena. Aaron has been concerned that Serena leans emotionally more on Dan than him. He asks her to come with him to Buenos Aires for Christmas. Serena asks Dan for his opinion, and he tells her to go. At Eleanor's wedding however, Dan confronts Serena about his feelings for her. Because she knows about her mother and Rufus' relationship, and because she has already said yes to Aaron, Serena turns Dan down and goes ahead with Aaron's trip. Serena breaks up with Aaron during the holiday and Dan and Serena meet with each other and they both decide there are better off back together. Dan soon learns he shares a sibling brother with Serena and becomes ridden with guilt when Rufus asks him to let Lily tell Serena the news. Serena and Dan attempt to return to normal, but find this difficult with Lily and Rufus, who have decided to go public with their relationship. Dan, and Serena both get acceptance letters to Yale but Serena decides that Yale isn't for her and applies to Brown and gives her spot to Blair who was wait-listed. A new teacher named Ms. Carr teaches at Constance Billard and there is an obvious attraction between them. Blair is so willing to get back at Ms. Carr for giving her a B on a paper that she sends in a rumor to Gossip girl concerning a secret relationship going on between Dan and Ms. Carr. Serena herself is becoming suspicious when she sees Dan and Ms. Carr discussing Dan's paper together but believes Dan when he says nothing is going on between the two of them. Serena then sees Dan and Ms. Carr in a coffee shop together. She cannot hear what they are saying but in fact Dan is only comforting Ms. Carr who is in tears about the slanderous teacher-student relationship rumor. Serena captures a photo of Dan touching Ms. Carr's face in an intimate way and shares the photo with Blair although she has doubts about the authenticity of the situation. Blair enters a parent-teacher meeting at Constance Billard and presents the incriminating photo at hand. Dan explains to Serena nothing happened between him and Ms. Carr but it is too late. Ms. Carr is fired. Serena and Dan's relationship hits another dead end when things become too much for them to take. First their parents start dating, then they find out they shared a half brother together, and now the mess of the rumor. Serena goes to apologize to Ms. Carr while admitting regretfully that she was the one who gave the photo to Blair. Later Dan visits Ms. Carr and starts to apologize for how things went down but then she kisses him. Dan, at first, is surprised at her actions. Ms. Carr points out that she doesn't teach at Constance anymore so there is no student-teacher relationship. So Dan obliges and they have sex in the dark of the room. Season 3 Dan joins Blair, Vanessa and Georgina at NYU and instantly fits in amongst many aspiring writers. His stay at NYU also tests his friendship with Vanessa, who assumes that Dan has been absent in their friendship ever since he became wealthy. Dan explains to Vanessa that he and his family are still adjusting to their nouveau-riche status and Vanessa leaves frustrated at Dan. Dan's first day at NYU reveals Georgina Sparks' return. When Georgina throws a party, Blair's attempt at sabotage results in Dan standing up for Georgina and with Dan becoming popular at NYU, leaving Blair ostracized. Dan and Georgina's relationship is short-lived in the episode "The Lost Boy". Georgina has Blair in a wild goose chase to enter an elite secret society that gets her into a bidding war with Chuck Bass at an auction. Serena recognizes Georgina's handwriting in Blair's invitation to that secret society and confronts her. The Humphrey family leaves and Georgina is left alone at the auction. Serena reveals Georgina's scheming to Dan and Dan ends his relationship with Georgina. Georgina leaves for Boston when she discovers that Scott, Vanessa's boyfriend, is Rufus and Lily's lovechild and that Vanessa had known that he was for a long time. In "Dan de Fleurette", Dan moves on from his relationship with Georgina when he meets Olivia, a movie star who attended NYU to be a normal college student. Dan first meets Olivia, who calls herself Kate until her movie premiere of Fleur reveals that she is Olivia Burke, a Hollywood movie star. Olivia apologizes to Dan and they embark in a new relationship. Georgina's return from Boston has her blackmailing Vanessa when she discovers that Dan has moved on from their relationship so quickly in "Rufus Getting Married". Dan, then persuades Vanessa to reveal her secret, only to find out that Scott Ronson is his half-brother, the lovechild of Rufus and Lily. Rufus and Lily's wedding has Dan and Vanessa reluctant to tell the truth about Scott. On Rufus and Lily's wedding when Lily gets cold feet, Rufus confronts her with Scott unknowingly asking if their wedding was off. Lily scolds Scott and Georgina reveals that Scott is their lovechild. Dan arrives with the rest of the family and confirms Georgina's statement. Dan and Blair find Georgina eating the wedding cake and Blair leaving. At the end of the episode, Dan expresses regret that Georgina left unscathed. Blair assures him that she didn't by sending Dorota and Vanya to get rid of her. Dan and Olivia encounter several troubles in their relationship when Vanessa alienates them both during her attempt at getting the freshman toast at NYU. When Dan introduces Olivia to Rufus and Lily, she starts acting like a stereotypical movie star towards them until Vanessa reveals that she lied to the both of them so that Olivia wouldn't have to meet her judgmental mother, Gabriela. Vanessa loses the toast to Olivia and properly reintroduces Olivia the next morning after the incident. Olivia's movie star background also catches up to her when she is forced to continue her fake relationship with Patrick Roberts, her former co-star. Serena intervenes and Dan and Olivia soon manage to make their relationship public. Dan and Olivia's relationship soon comes to an end when Olivia is again forced back into the world of film and return to Hollywood but not without Dan and Vanessa giving her the best college experience. The college experience results in a threesome that consequently leads to Dan and Olivia's break-up when Olivia states that Dan has feelings for Vanessa. Vanessa unfortunately, falls for theater student, Paul Hoffman. With Olivia gone, Dan embarks on a new relationship with Vanessa, confessing his love for her during Bart Bass' death anniversary and Vanessa turning him down. Dan attempts to impress Vanessa by impressing Gabriela that ends with Gabriela telling Dan that if he breaks Vanessa's heart, their friendship wouldn't make it. Vanessa eventually reveals her feelings for Dan in a beach party when Dan arrives with a fresh date and Vanessa getting back together with Paul Hoffman. Dan had been unaware that Vanessa had ended her relationship with Paul until Paul and Dan's date reveals each others' predicaments, get together and leave Dan and Vanessa at the party. Dan and Vanessa reveal their feelings toward each other and kiss at the end of the episode. Dan finds little trouble with his relationship with Vanessa and reveals their relationship to Rufus. Vanessa, frustrated at the lack of something different in their relationship, heeds Nate's advice on role-playing and sets up a date fashioned according to Dan's favorite movie Rear Window. Vanessa is not convinced at Dan appreciating what she did for her date, leaves. Dan confronts her and tells her that their relationship is different from their friendship. Dan applies to get into Tisch's writing program as Vanessa reads and secretly critiques one of the stories that he plans on submitting for admission. Dan secretly read Vanessa's film script and is impressed, unaware that Vanessa is also applying for the same program. Towards the end of the season, Vanessa decides to accept an internship with CNN, that of which requires her to go on a six month trip to Haiti. Despite this, the two of them decide that they can still maintain their relationship as a long-distance one. In the season finale, Dan wakes up with Serena in his bed. The viewers learn that the two did not sleep together but - after staying up until 4AM talking and drinking wine - they shared a kiss, that of which Serena classifies as them "falling into a comfortable path for one...or ten minutes". When Dan hears that Serena breaks up with Nate, he calls her, possibly to say he had feelings for her.When she announces she won't be back to talk to him till September he appears very disappointed. He then shuts the e-mail he had opened to write to Vanessa, his current girlfriend, who is no longer taking his calls (due to Nate's interception after finding out from Gossip Girl's blast and later overhearing at the hospital about the kiss). When he later learns that Serena is going to Paris with Blair, he goes online to book a ticket. Before he can, however, Georgina visits Dan and tells him that she's pregnant with his child. Season 4 Georgina had her son, Milo, on July 7, 2010. She later goes on to say that she did a paternity test in order to prove that Dan was the father. However, it is later revealed to be another one of her ploys for revenge when she leaves Dan alone with Milo, never to be heard from or seen again. She left a note saying that she went to the "spa". In the “Double Identity” episode, Rufus finds Milo’s ID bracelet, which says that Milo has a different blood type than Dan. Dan and Vanessa slept together, after Nate told Vanessa (with Juliet’s help) that Dan still has feelings for her. In the end of the episode, Dan admits to Vanessa that he still has feeling for her, since Gossip Girl said Serena was back in town. In the "The Undergraduates" episode, Georgina comes back from the "spa" (St. Barts) to tell Dan about Serge, Milo's real father, and to say that she and Milo are going to live with Georgina's parents. Dan is sad to see Milo leave. Vanessa move in with Dan. In the "Touch of Eva", Blair, Serena and Dan found out that Eva was a prostitute. Dan tells Nate about Eva. Nate then tells Chuck about Eva. Chuck confronts Eva but forgives her later on. Frustrated, Blair look at other means to get rid of Eva, which she succeeded in. Eva leaves and Chuck is torn. Chuck confronts Blair and declares war. Dan found out he still had feelings for Serena, but eventually went back to Vanessa. Serena is seen lying on her bed alone, depressed. While Serena's in rehab, Dan goes to visit her and she tells him that she picked him and not Nate and at the end of Gaslit they kiss. Blair finds out Juliet was behind Serena's overdose and enlists Dan's help in clearing Serena's name. The two embark on a road trip to Connecticut to track down Juliet. After discovering that Juliet's brother, Ben, was a teacher at Serena's former boarding school, the twosome return to Manhattan armed with this new information, only to discover that Serena has already taken matters into her own hands. Over winter break, Dan and Blair find themselves alone together in New York, and end up attending a screening of "Nanette" at Film Forum together. Though they were intent on this secret rendezvous being a one-time occurrence, the two soon find themselv es repeatedly making plans to spend time together. Dan and Blair's budding friendship is challenged when they discover that they're now rival interns at W magazine. Blair admits to Serena that Dan is her only true competition in the internship, as he has proven himself her equal. Blair considers sabotaging Dan, but decides against it. However, Dan, assuming Blair would stick to the pact, sabotages her. Once Blair finds out, she attacks Dan at the party, and they both end up getting fired. Later, when Dan finds out how hard Blair worked to get the internship, he tells their supervisor that he was to blame, and gets Blair her dream job back. Dan asks Blair for help in getting an article he's written to editors at other Conde Nast publications, which Blair refuses to do. While talking to Eric, Dan admits he wants to spend Valentine's Day with Blair, but says it's just because he needs her help. Later, at a Valentine's Day party, Dan follows Blair while she is looking for Chuck. When Chuck walks in with Raina Thor pe, Dan and Blair hide, and Blair learns that Chuck has real feelings for Raina. Dan sits with Blair and takes her hand in his, trying to comfort Blair. She later calls him and says that she enjoyed his article and gave to an editor at another magazine. The two spend the rest of Valentine's Day on the phone together, while watching Rosemary's Baby in their own beds. When Blair begins to overextend herself, Dan offers to help her as a friend, but only if she admits that she needs him. She initially refuses, but eventually gives in. Later that night, she comes to the loft and tells him that she was "fired/quit" from the magazine because she was "imploding". Dan once again comforts her by asking her to stay. They end up falling asleep together on the couch while watching a movie. Dan reluctantly goes along with Blair's plan to keep their newfound friendship a secret. However, Dorota becomes suspicious of Blair being particularly cheerful (as a result of spending time with Dan), and when she finds a magazine of Dan's in her bedroom, she accuses them of having an affair. Then, when Dan receives some surprising advice from his dad about his secret relationship with Blair, he begins to wonder if there could be something more going on between him and Blair. In order to convince people that they're not falling for each other, Dan and Blair agree to announce their friendship during a party. But they don't get a chance when their friends are distracted by Lily turning herself into the police, and they reluctantly decide to end their friendship. However, Dan arrives at Blair's home late r that night and suggests that they should confront the possibility that they actually are falling for each other with a kiss. After a long hesitation, Blair finally pulls Dan to her and kisses him. While the kiss made Dan realize he has for feelings for Blair, which he eagerly wants to discuss with her, Blair spends the week following the kiss in her room (afraid to face how the kiss made her feel). While working at a photoshoot for prominent families, Blair tells her former supervisor at W, Epperly, that she recently shared a "life changing" kiss with someone, who immediately tells Chuck. Chuck then goes over to the loft to see if Dan might know who Blair kissed. Dan is clearly excited when he hears the kiss was "life changing" for Blair. By the end of the conversation, Chuck realizes it was Dan Blair kissed. He gets Dan invited to the photoshoot to be humiliate him in front of Blair. When Dan and Blair confront Chuck about it, he says he knows that they kissed. Blair claims that it made her realize she should be with Chuck (which clearly upsets Dan), but Chuck's actions make Blair realize that they shouldn't be together. Dan is hired to cover the Prince Louis' visit to Manhattan. But, when he discovers that Louis is with Blair, he backs out of the job. In order to help the pair to maintain their secrecy, Dan and Blair stage a kiss at the Pink Party to be witnessed by an adviser of Louis' , in order to convince him they're dating. Meanwhile, Serena has become aware of Dan and Blair's first kiss, and has had her cousin Charlie follow Dan. Charlie follows Dan and Blair at the party, records them making out, and sends it to Gossip Girl. Serena confronts Dan and Blair about their relationship, and they say they've only been hiding that they're friends. When asked about their first kiss, Dan and Blair tells Serena it was just an experiment. When Serena is still upset with them, Dan walks out. Blair then argues with Serena, telling her that she and Dan have a genuine connection that has nothing to do with Serena. Later that night, Charlie comes to the loft to apologize to Dan for exposing him and Blair. She says she could tell by the kiss that Dan really likes Blair. Dan agrees with her and says he never expected he'd have feelings for her. Appearance and Style Dan is often seen in casual clothes, in Season 1 he expressed his dislike for tuxes and suits. He often wears jeans and a t-shirt, a fact that Jenny tells Serena when asked what to wear for their first date. Dan has been known to dress up when needed though, such as when he goes to parties or important social events. As the Seasons progress and he becomes a part of the van der Woodsen family Dan starts to wear more designer clothes; he has a designer wallet which Vanessa notices. Personality Dan is very sarcastic, funny, witty, knowledgeable and has a huge sense of justice (a good guy type). He strongly cares about his family, especially about his little sister, Jenny. Dan is stoically loyal and fiercely protective of his friends and family. But despite generally having a good heart and good intentions, he has his share of flaws. Dan has a tendency to be overly judgemental and he can be self-righteous. Family TV Series *Rufus Humphrey - (Father) *Alison Humphrey - (Mother) *Jenny Humphrey - (Sister) *Scott Ronson - (Half-Brother) *Lillian Bass Humphrey - (Step-Mother) *Serena van der Woodsen - (Step-Sister) *Eric van der Woodsen - (Step-Brother) *Chuck Bass - (Adoptive Step-Brother) Romantic Relationships Novel Series *Serena van der Woodsen *Vanessa Abrams TV Series *Serena van der Woodsen - (ex-girlfriend, first love) *Rachel Carr - (fling) *Olivia Burke - (ex-girlfriend) *Vanessa Abrams - (ex-girlfriend, ex-best friend) *Blair Waldorf - (in love with, kissed twice, best friend) Books Dan has written some books over the years though only Inside has been published. Quotes Dan: "I've been walking around the city all night with one all-consuming, paralyzing thought." Eric: "Do you like her?" Dan: "What? No no no. I don't like her. No, of course not. Not at all. I'm just curious. And you know, I mean, she does... she does smell nice." Eric: "Oh, you are ass backwards crushing on Blair Waldorf!" Blair: What if i lose everything? Dan: You'll still have me. Blair:Do you think it wouldn't matter if my baby is another man's child? Dan: It wouldn't to me. Serena:You mean you were gonna tell her you love her Dan: Inspite of my self, ad honestly, many times, inspite of her. I mean, I didn't want to. I kept trying to make it go away, but how do you kill a feeling? Photos This character has a Photo Gallery. Category:Males Category:Characters Category:Main Characters Category:Books Category:Character Galleries Category:People